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US4629732A - Fungicidally active 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols - Google Patents

Fungicidally active 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols Download PDF

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Publication number
US4629732A
US4629732A US06/600,581 US60058184A US4629732A US 4629732 A US4629732 A US 4629732A US 60058184 A US60058184 A US 60058184A US 4629732 A US4629732 A US 4629732A
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Prior art keywords
methyl
butan
imidazol
trifluoromethylthio
triazol
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US06/600,581
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English (en)
Inventor
Udo Kraatz
Erich Klauke
Gerhard Jager
Karl H. Buchel
Paul-Ernst Frohberger
Wilhelm Brandes
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to certain new 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols, to a process for their preparation and to their use as fungicides.
  • the present invention now provides, as new compounds, the 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols of the general formula ##STR2## in which Az represents 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl or imidazol-1-yl,
  • B represents the keto group or the CH(OH) group
  • Y represents oxygen or sulphur
  • R represents halogenoalkyl, optionally substituted phenyl or optionally substituted benzyl, or, provided Y represents sulphur, may represent alkyl, and
  • X 1 , X 2 and X 3 are selected independently and each represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulphonyl, nitro, cyano, alkoxycarbonyl or optionally substituted phenyl,
  • the invention also provides a process for the preparation of a 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-one or -ol of the formula (I), in which a halogenoether ketone of the general formula ##STR3## in which Hal represents halogen, preferably chlorine or bromine, and
  • the new 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols of the formula (I) have powerful fungicidal properties.
  • the compounds according to the invention surprisingly exhibit a better fungicidal action than the 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-ones and -ols which are known from the state of the art and are similar compounds chemically and with respect to their action.
  • the new 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols of the formula (I) are interesting intermediate products for the preparation of further active compounds for plant protection.
  • functional derivatives of the keto group can be obtained, for example oximes, oxime-ethers, hydrazones and ketals.
  • the compounds of the formula (I) can be converted in the customary manner, at the hydroxyl group, into the corresponding ethers, or acyl or carbamoyl derivatives can be obtained by reaction with, for example, acyl halides or carbamoyl chlorides, in a manner which is in principle known.
  • Formula (I) gives a general definition of the 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols according to the invention.
  • this formula
  • R represents halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or optionally substituted phenyl or benzyl, the phenyl substituent in either case being selected from halogen, alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, nitro, cyano, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, and phenyl which is optionally substituted by halogen; or provided Y represents sulphur, R may represent straight-chain or branched alkyl having 1 to 6 carbon atoms,
  • X 1 represents hydrogen, halogen, alkyl, alkoxy, alkylthio or alkylsulphonyl each having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, nitro, cyano, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, or phenyl which is optionally substituted by halogen,
  • X 2 represents hydrogen, halogen, alkyl, alkoxy, alkylthio or alkylsulphonyl each having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, nitro, cyano, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, or phenyl which is optionally substituted by halogen, and
  • X 3 represents hydrogen, halogen, alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.
  • R represents halogenoalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms (especially phenyl or benzyl, the or phenyl substituent being in either case selected from fluorine, chlorine, methyl, ethyl, isopropyl, tert.-butyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, nitro, cyano and phenyl which is optionally substituted by fluorine and/or chlorine; or R may represent straight-chain or branched alkyl having 1 to 4 carbon atoms, provided Y represents sulphur,
  • X 1 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, tert.-butyl, methoxy, methylthio, methylsulphonyl, trifluoromethyl, nitro, cyano, methoxycarbonyl, ethoxycarbonyl or phenyl which is optionally substituted by fluorine and/or chlorine,
  • X 2 represents hydrogen, fluorine, chlorine, methyl, ethyl, isopropyl, tert.-butyl, methoxy, methylthio and trifluoromethyl, and
  • X 3 represents hydrogen, fluorine, chlorine or methyl.
  • Formula (II) gives a general definition of the halogenoether ketones to be used as starting materials in carrying out the process according to the invention.
  • R, X 1 , X 2 , X 3 and Y preferably represent those radicals which have already been mentioned, in connection with the description of the compounds of the formula (I), as being preferred for these substituents.
  • halogenoether ketones of the formula (II) have not hitherto been disclosed in the literature. However, they can be obtained by known processes in which, for example, known phenols of the general formula ##STR7## in which X 1 , X 2 and X 3 have the meanings given above, are reacted with a halogenoketone of the general formula ##STR8## in which Y and R have the meanings given above and
  • Hal' represents chlorine or bromine.
  • halogenoketones of the formula (IV) have not hitherto been disclosed in the literature. However, they form the subject of United States Application Ser. No. 328,871, filed Dec. 8, 1981, abandoned. They are obtained by a process in which ketones of the general formula ##STR9## in which R and Y have the meaning given above,
  • an inert organic solvent for example ether or a chlorinated or non-chlorinated hydrocarbon, at room temperature, or with a customary chlorinating agent, for example sulphuryl chloride, at from 20° to 60° C.
  • ketones of the formula (V) are known (see, for example, U.S. Pat. No. 3,937,738), and some of them form the subject of U.S. Application Ser. No. 328,871, filed Dec. 8, 1981, supra. They can be obtained by the process given in the reference, for example, by reacting keto derivatives of the general formula ##STR10## in which Z represents chlorine, bromine or the group
  • R 1 represents alkyl having 1 to 4 carbon atoms or optionally substituted phenyl
  • R and Y have the meanings given above and
  • M represents an alkali metal, preferably sodium and potassium, or hydrogen
  • the compounds of the formula (VII) are generally known compounds of organic chemistry and are employed in situ, if appropriate.
  • Inert organic solvents are suitable as diluents for the reaction according to the present invention.
  • These solvents include, as preferences, ketones, such as diethyl ketone and, in particular, acetone and methyl ethyl ketone; nitriles, such as propionitrile and, in particular, acetonitrile; alcohols, such as ethanol or isopropanol; ethers, such as tetrahydrofuran or dioxane; benzene; toluene; formamides, such as, in particular, dimethylformamide; and halogenated hydrocarbons.
  • ketones such as diethyl ketone and, in particular, acetone and methyl ethyl ketone
  • nitriles such as propionitrile and, in particular, acetonitrile
  • alcohols such as ethanol or isopropanol
  • ethers such as tetrahydrofuran or dioxane
  • the reaction according to the invention is carried out in the presence of an acid-binding agent.
  • an acid-binding agent Any of the inorganic or organic acid-binding agents which can customarily be used can be added, such as alkali metal carbonates, for example sodium carbonate, potassium carbonate and sodium bicarbonate, or such as lower tertiary alkylamines, cycloalkylamines or aralkylamines, for example triethylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine and N,N-dimethylbenzylamine, and furthermore pyridine and diazabicyclooctane.
  • An appropriate excess of azole is preferably used.
  • reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at between 20° and 150° C., preferably at from 60° to 120° C. When a solvent is present, the reaction is advantageously carried out at the boiling point of the particular solvent.
  • 2 to 4 mols of azole and 1 to 4 mols of acid-binding agent are preferably employed per mol of the compound of the formula (II).
  • the solvent is distilled off, and the residue is taken up with an organic solvent and washed with water. The organic phase is dried over sodium sulphate and freed from solvent in vacuo.
  • the residue is purified by distillation or recrystallization, or by salt formation and recrystallization.
  • the reduction according to the invention may be effected in a customary manner, according to known methods, for example by reaction with a complex hydride, if appropriate in the presence of a diluent, or by reaction with aluminum isopropylate in the presence of a diluent.
  • a polar organic solvent is suitable as the diluent for the reaction according to the invention.
  • solvents include, as preferences, alcohols, such as methanol, ethanol, butanol and isopropanol, and ethers, such as diethyl ether or tetrahydrofuran.
  • the reaction is carried out at from 0° to 30° C., preferably at from 0° to 20° C.
  • a complex hydride such as sodium borohydride or lithium alanate
  • the residue is taken up in dilute hydrochloric acid, and the solution is then rendered alkaline and extracted with an organic solvent. Further working-up is effected in a customary manner.
  • reaction temperatures can be varied within a relatively wide range; in general, the reaction is carried out at between 20° and 120° C., preferably at from 50° to 100° C.
  • hydrogen halide acids for example hydrobromic acid and, in particular, hydrochloric acid
  • phosphoric acid for example hydrobromic acid and, in particular, hydrochloric acid
  • phosphoric acid for example hydrobromic acid and, in particular, hydrochloric acid
  • phosphoric acid for example hydrobromic acid and, in particular, hydrochloric acid
  • the acid-addition salts of the compounds of the formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, for example hydrogen chloride, and they can be isolated in a known manner, for example by filtration, and if appropriate purified by washing with an inert organic solvent.
  • Salts of metals of main groups II to IV and of subgroups I and II and IV to VIII are preferably used for the preparation of metal-salt complexes of the compounds of the formula (I), examples of metals which may be mentioned being copper, zinc, manganese, magnesium, tin, iron and nickel.
  • Preferred anions of the salts are those which are derived from the following acids: hydrogen halide acids (for example hydrochloric acid and hydrobromic acid), phosphoric acid, nitric acid and sulphuric acid.
  • the metal-salt complexes of the compounds of the formula (I) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol, and adding the solution to the compound of the formula (I).
  • the metal salt complexes can be isolated in a known manner, for example by filtration, and if appropriate purified by recrystallization.
  • the active compounds according to the invention exhibit a powerful microbicidal action and can be employed in practice for combating undesired micro-organisms.
  • the active compounds are suitable for use as plant protection agents.
  • Fungicidal agents in plant protection are employed for combating Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • the good toleration, by plants, of the active compounds, at the concentrations required for combating plant diseases permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with particularly good success for combating those fungi which cause powdery mildew diseases, thus, for combating Erysiphe species, for example against the powdery mildew of barley or cereal causative organism (Erysiphe graminis) and the powdery mildew of cucumber causative organism (Erysiphe cichoracearum), or for combating Podosphaera species, for example against the powdery mildew of apple causative organism (Podosphaera leucotricha); and in addition for combating rice disease causative organisms, for example Pellicularia sasakii.
  • Erysiphe species for example against the powdery mildew of barley or cereal causative organism (Erysiphe graminis) and the powdery mildew of cucumber causative organism (Erysiphe cichoracearum)
  • Podosphaera species for example against the powdery mildew of apple causative organism
  • the substances according to the invention When used in appropriate quantities, the substances according to the invention also exhibit plant growth-regulating properties.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans or fumigating coils, as well as ULV cold mist and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans or fumigating coils, as well as ULV cold mist and warm mist formulations.
  • formulations may be produced in known manner, for example by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • extenders that is to say liquid or liquefied gaseous or solid diluents or carriers
  • surface-active agents that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid diluents or carriers especially solvents
  • aromatic hydrocarbons such as xylene, toluene or alkyl naphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic or alicyclic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions
  • alcohols such as butanol or glycol as well as their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethylsulphoxide, as well as water.
  • liquefied gaseous diluents or carriers liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • ground synthetic minerals such as highly-dispersed silicic acid, alumina and silicates.
  • crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • non-ionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products.
  • Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.
  • Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations in general contain from 0.1 to 95 percent by weight of active compound, preferably from 0.5 to 90 percent by weight.
  • the active compounds according to the invention can be present in the formulations or in the various use forms as a mixture with other active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellents, growth factors, plant nutrients and agents for improving soil structure.
  • active compounds such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellents, growth factors, plant nutrients and agents for improving soil structure.
  • the active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They may be used in the customary manner, for example by watering, immersion, spraying, atomizing, misting, vaporizing, injecting, forming a slurry, brushing on, dusting, scattering, dry dressing, moist dressing, wet dressing, slurry dressing or encrusting.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
  • active compound in general 0.001 to 50 g, preferably 0.01 to 10 g, are employed per kilogram of seed.
  • active compound concentrations of in general 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are employed at the place of action.
  • the present invention also provides a fungicidal composition containing as active ingredient a compound of the present invention in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
  • the present invention also provides a method of combating fungi which comprises applying to the fungi, or to a habitat thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture with a diluent or carrier.
  • the present invention further provides crops protected from damage by fungi by being grown in areas in which immediately prior to and/or during the time of the growing a compound of the present invention was applied alone or in admixture with a diluent or carrier.
  • Example 1 10 g (0.026 mol) of 1-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-one (Example 1) were dissolved in 100 ml of methanol and 1 g (0.025 mol) of sodium borohydride was added in portions to the solution. The reaction mixture was further stirred at room temperature for 30 minutes and was thereafter introduced into water. The mixture was extracted with methylene chloride, and the organic phase was dried over sodium sulphate and concentrated in vacuo. The residue crystallized after a short time.
  • the fungicidal activity of the compounds of this invention is illustrated by the following biotest examples.
  • Emulsifier 0.25 part by weight of alkylaryl polyglycol ether
  • the plants were placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote the development of powdery mildew pustules.
  • the active compounds were used as dry dressings. These are prepared by extending the particular active compound with a ground mineral to give a finely pulverulent mixture, which ensured uniform distribution on the seed surface.
  • the seed was shaken with the dressing in a closed glass flask for 3 minutes.
  • the plants were placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% in order to promote the development of powdery mildew pustules.
  • Emulsifier 0.3 part by weight alkylaryl polyglycol ether
  • the plants were then placed in a greenhouse at 23° to 24° C. and at a relative atmospheric humidity of about 75%.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US06/600,581 1981-05-15 1984-04-17 Fungicidally active 3-substituted 1-azolyl-3-methyl-1-phenoxy-butan-2-ones and -ols Expired - Fee Related US4629732A (en)

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DE3119390 1981-05-15
DE19813119390 DE3119390A1 (de) 1981-05-15 1981-05-15 3-substituierte 1-azolyl-3-methyl-1-phenoxy-butan-2-one und -ole, verfahren zu iher herstellung und ihre verwendung als fungizide

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US (1) US4629732A (de)
EP (1) EP0065204B1 (de)
JP (1) JPS57193464A (de)
AT (1) ATE17478T1 (de)
BR (1) BR8202823A (de)
CA (1) CA1177835A (de)
DE (2) DE3119390A1 (de)
DK (1) DK220482A (de)
HU (1) HU187700B (de)
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ZA (1) ZA823342B (de)

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Publication number Priority date Publication date Assignee Title
GB8326210D0 (en) * 1983-09-30 1983-11-02 Fbc Ltd Azole compounds

Citations (6)

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FR2360309A1 (fr) * 1976-08-07 1978-03-03 Bayer Ag Composition anti-microbienne contenant des derives de 1-azolyl-4-hydroxy-butane
US4123542A (en) * 1977-01-19 1978-10-31 Syntex (U.S.A.) Inc. Derivatives of N-alkyl imidazoles
US4154842A (en) * 1976-08-07 1979-05-15 Bayer Aktiengesellschaft Fungicidally and bactericidally active 1-azolyl-4-hydroxy-1-phenoxy-butane derivatives
US4215127A (en) * 1978-11-02 1980-07-29 The Dow Chemical Company Substituted 1-phenoxy-1-triazolyl-2-butanone compounds and their use as fungicides
EP0049111A1 (de) * 1980-09-25 1982-04-07 Ishihara Sangyo Kaisha Ltd. Phenoxybutyltriazol-Derivate, diese enthaltende fungizide Zusammensetzung für Landwirtschaft und Gartenbau und Verfahren zu ihrer Herstellung
US4406909A (en) * 1980-06-07 1983-09-27 Bayer Aktiengesellschaft Combating fungi with 4-substituted 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-ones and -ols

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2360309A1 (fr) * 1976-08-07 1978-03-03 Bayer Ag Composition anti-microbienne contenant des derives de 1-azolyl-4-hydroxy-butane
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ATE17478T1 (de) 1986-02-15
DE3119390A1 (de) 1982-12-09
BR8202823A (pt) 1983-04-26
EP0065204A3 (en) 1984-01-04
EP0065204B1 (de) 1986-01-15
ZA823342B (en) 1983-03-30
IL65754A (en) 1985-12-31
DE3268498D1 (en) 1986-02-27
DK220482A (da) 1982-11-16
JPS57193464A (en) 1982-11-27
CA1177835A (en) 1984-11-13
HU187700B (en) 1986-02-28
IL65754A0 (en) 1982-08-31
EP0065204A2 (de) 1982-11-24

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